I mistook the planning for progress

I message my friend once a year, on her birthday. Today she told me she'd quit her job.


My friend hides her birthday on Facebook, but I’ve had the date saved in my calendar for years and every year I message her on it. That message is the only conversation we have all year. Today she turned 30.

We did the usual update, work and family, and then she told me she had quit her job because she felt lost. This is someone who was near the top of everything at school and went to good universities, and someone I would bet on before I’d bet on myself. She told me she had started a business, it failed, and now she has another one she wants to start. But she has not started it yet.

She sounded certain when she described it. Not hopeful. Certain. I told her it sounded like she already knew exactly what she needed to do, and that something else was standing in the way. She said that was exactly it. It isn’t a shortage of ability. It’s that she overthinks everything.

I remembered something Chris Williamson said: if your life was a movie, and the audience had watched it up to this point, what would they be screaming at the screen? I was sitting in the audience of her movie, and I knew the line before she had finished the sentence. Start it. Today.

I could see the same thing in myself. I have started a business and it failed. I want to start another one, and I know I would do it better this time, but the fear of failing again has me overthinking every part of it.

So instead of starting, I did what I have always done. I spent my entire 20s planning, and I mistook the planning for progress. All that thinking never made me braver. It made me more lost, probably the same way she is lost. I ended up with a plan and no confidence to do any of it.

I don’t want to turn 40 and find that I spent my 30s the same way I spent my 20s. So I’ve put myself in the audience of my own movie. That’s the plan now, and it’s the whole plan: start today and take one small step right after another, so I find out what happens next instead of sitting here rehearsing it.

I don’t know yet whether the overthinking stops once I start. I know it doesn’t stop while I wait.

This is the first article I’ve published here, and I’m doing it before I have anything to show for it.

In high school I would have bet on her before I’d bet on myself, and this time I’d bet on both of us.